Art

J-GLOBAL ID：200902249462959311   Reference number：04A0494107

Synthesis of (R)-(+)-Tanikolide through Stereospecific C-H Insertion Reaction of Dichlorocarbene with Optically Active Secondary Alcohol Derivatives

ジクロロカルベンの光学活性第二アルコール誘導体との立体特異的C-H挿入反応を経る(R)-(+)-タニコリドの合成

Author (4)： ARASAKI H (Gifu Pharmaceutical Univ., Gifu, JPN) ,  IWATA M (Gifu Pharmaceutical Univ., Gifu, JPN) ,  MAKIDA M (Gifu Pharmaceutical Univ., Gifu, JPN) ,  MASAKI Y (Gifu Pharmaceutical Univ., Gifu, JPN)
Material： Chemical and Pharmaceutical Bulletin  (Chemical & Pharmaceutical Bulletin)
Volume： 52  Issue： 7  Page： 848-852  Publication year： Jul. 01, 2004 
JST Material Number： G0504A  ISSN： 0009-2363  CODEN： CPBTAL  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *lactone ,...
Semi thesaurus term： dichlorocarbene ,...

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JST classification (1)： Pyranes  (CF07092R)

Substance index (19)： (+)-Tanikolide ,  Dichlorocarbene ,  Chloroform ,  Hexadecyltrimethylammonium chloride ,  Mannitol ,  (2R)-2,3-Isopropylidenedioxypropanal ,  (4S)-2,2-Dimethyl-4β-undecyl-1,3-dioxolane ,  (4S)-2,2-Dimethyl-1,3-dioxolane-4β-propionic acid ethyl ester ,  (4S)-2,2-Dimethyl-4α-(dichloromethyl)-4-undecyl-1,3-dioxolane ,  (2S)-2-(Dichloromethyl)-1,2-tridecanediol ,  (2S)-1-(tert-Butyldiphenylsiloxy)-2-(dichloromethyl)-2-tridecanol ,  (4S)-2,2-Dimethyl-4-(dichloromethyl)-1,3-dioxolane-4β-propionic acid ethyl ester ,  (5S)-5α-(Dichloromethyl)-5-(hydroxymethyl)tetrahydrofuran-2-one ,  (5S)-5α-(Dichloromethyl)-5-(tert-butyldiphenylsiloxymethyl)tetrahydrofuran-2-one ,  (4S)-2,2-Dimethyl-4-(dichloromethyl)-1,3-dioxolane-4β-propionaldehyde ,  (4S)-2,2-Dimethyl-4α-(chloromethyl)-4-undecyl-1,3-dioxolane ,  (4S)-2,2-Dimethyl-4α-methyl-4-undecyl-1,3-dioxolane ,  (2R)-2-Undecyloxirane-2β-carbaldehyde ,  (2R)-2α-Undecyl-2-(tert-butyldiphenylsiloxymethyl)oxirane

Reference (54)：

• 1) Representative examples of biologically active tertiary alcohol derivatives, Cinatrin C, Integerrimine, Harringtonine, K-252a, Forstriecin, Viridiofungin, Erythromicin, and Zaragozic acid: References cited in the literature, Evans D. A., Burgey C. S., Kozlowski M. C. Tregay S. W., J. Am. Chem. Soc., 121, 686—699 (1999).
• 2) Henegar K. E., Ashford S. W., Baughan T. A., Sih J. C., Gu R.-L., J. Org. Chem., 62, 6588—6597 (1997).
• 3) Jimenez O., Busch M. P., Guerrero A., J. Org. Chem., 62, 3496—3499 (1997).
• 4) Doyle M. P., Oeveren A. V., Westrum L. J., Protopopova M. N., Clayton T. W., Jr., J. Am. Chem. Soc., 113, 8982—8984 (1991).
• 5) Reineke W., Otting W., Knackmuss H.-J., Tetrahedron, 34, 1707—1714 (1978).

Terms in the title (6)： ジクロロカルベン ,  光学活性 ,  第二アルコール ,  誘導体 ,  挿入反応 ,  タニコリド